Tetrahedron

Novel formation of indoles and 3, 1-benzoxazines from o-alkenylanilides and dimethyl (methylthio) sulfonium trifluoromethanesulfonate

K Okuma, T Yasuda, I Takeshita, K Shioji, Y Yokomori

Index: Okuma, Kentaro; Yasuda, Takumi; Takeshita, Itsuki; Shioji, Kosei; Yokomori, Yoshinobu Tetrahedron, 2007 , vol. 63, # 34 p. 8250 - 8254

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Citation Number: 15

Abstract

The reaction of dimethyl (methylthio) sulfonium trifluoromethanesulfonate (DMTST) with o- allylphenol gave 2-methylthiomethyl-2, 3-dihydrobenzofuran in 97% yield. The reaction of DMTST with N-tosyl-o-isopropenylanilide followed by the addition of aq sodium carbonate afforded N-tosyl-3-methylindole in 88% yield, whereas N-tosyl-o-vinylanilide afforded N- tosylindoline in 85% yield.